Organizations, like any complex organism, have personalities, and I posit, can have personality shortcomings. Oftentimes this follows the personality of someone in leadership, someone of influence, or a combination of people. They can be overly cautious or reactive or distrustful or a hundred other things.
This tends to manifest as patterns that repeat themselves within the organization - think fractals - much like generational patterns in families. If the org (the organization, the organism) lacks the self-awareness to spot those fractals, they will continue indefinitely, for better or worse. Let's take a look at a few traits I have seen manifest in organizations.
Reactivity
- A trail of unfinished projects
- Teams regularly missing deadlines because they are busy putting out fires or estimating new potential projects.
- Rapidly accumulating technical debt, because there is never time to do things right or to go back & fix tech debt later.
The problem is that these companies end up spinning their wheels. So much time is spent context-switching & chasing short-term wins that essential long-term work never gets done.
There is a saying, attributed to a variety of people, which I repeat often to my teams: "Slow is smooth, smooth is fast". Frenetic action rarely saves time. In my experience, as pressure mounts, so does the tendency to become reactive. Perhaps because I just finished The Last Kingdom, I picture an army bracing for battle as the enemy charges. The commander screams, "Hold the line!" because being reactive in that situation means the enemy breaks through. The right course of action, even with existential organizational threats, is often to have the fortitude to stay the course set when heads were clearer. 
Like any personality attribute, reactivity exists because it is advantageous in some situations. For example, in an early startup, the ability to pivot quickly can mean the difference between the company surviving or failing. But, at a certain scale, it becomes a weakness. At scale, customers expect a certain level of polish to features, a certain level of reliability, a certain level of performance. Those things rarely come from quick & dirty solutions.
I would be remiss if I didn't mention something: reactive companies can be exciting - in the same way that adrenaline sports are exciting. They are exciting because there is a chance that things could go very badly. Those quick & dirty solutions breed a firefighting culture - exciting, and it will kill your company.
Resistance to Change
Self Preservation
I once sat in a meeting where I was grilled by a manager three levels above me regarding delays on his pet project, while the two levels of management between us sat gazing at the ceiling. This, in my opinion, is weak leadership. It is self-preservation at the expense of others.
After this event, I bemoaned to Charlie the fact that so few managers protect their people. He said something that surprised me. That behavior is similar to children of alcoholics. "What do I stand for? ... What do you want me to stand for? Or, what do I need to stand for in this situation to avoid getting hurt?" They stand for anything and nothing and won't stand up for their people if there is any risk to themselves.
In my opinion, that is a crucial role for a manager - giving their teams space to take risks without every move being scrutinized from on high. The weak managers were excellent politicians, able to play the chameleon to avoid attack.
The effect on the org is that they won't affect meaningful change if there is friction. This results in problematic patterns going unaddressed indefinitely.
In my experience, these leaders tend to be highly impersonal, rarely talking about their personal lives, their weaknesses, or their failures - because these things could be ammunition for a political opponent. There is, of course, some wisdom in that. However, they lack authenticity, and people tend not to trust them. I have far more respect for leaders who, while they have learned to be guarded, deliberately let their true selves shine through. True strength is not the ability to conceal weakness, but to succeed in spite of it.
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